Synthesis
Ethyl 2-(4-nitrophenyl)propionate (4.5 g, 20.17 mmol, 1.0 eq.) was used as raw material and dissolved in ethanol (40 ml). To this solution NaOH (1.614 g, 40.35 mmol, 2.0 eq.) and water (10 ml) were added. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and subsequently diluted with the addition of water. The pH of the reaction mixture was adjusted to acidic with dilute hydrochloric acid. The product was extracted with ethyl acetate, the organic layers were combined and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to give the crude product. Finally, the crude product was purified by column chromatography to give α-methyl-4-nitrophenylacetic acid (3.1 g, 78.8% yield). Mass spectrum (electrospray ionization): m/z 195.17 [M + H]+.
